1244 Pine Ave, Shady Side, MD 20764
Property image
Property image
FOR SALE
0.34 ACRES

$749,900

  • 4 Beds
  • 2 Baths
  • 2,674 sqft (on 0.34 acres)

1244 Pine Ave, Shady Side, MD 20764

Est. Mortgage $4,650/mo*
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Home Highlights

Single-Family Home
Built in 1950
0.34 acre lot
$280/sqft
2 Open Spaces

Local Information

  • Map ViewExplore the area around 1244 Pine Ave.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:New washer and dryerExceptional outdoor livingGenerous outdoor entertaining areasFully fenced backyardStainless steel appliancesNewer roof
Come Live the Bay Lifestyle! Welcome to 1244 Pine Avenue, a charming Chesapeake Bay retreat in Shady Side, Maryland, offering beautiful water and marina views, exceptional outdoor living, and the relaxed charm of coastal Maryland. Wake up to breathtaking sunrises, watch sailboats pass by, and enjoy peaceful evenings overlooking the bay. Located in the desirable Cedarhurst community, this inviting home offers the perfect opportunity to embrace waterfront living with a residents only marina across the street. Inside, the light filled living and dining areas feature a fireplace and expansive picture windows framing beautiful water views. The updated kitchen is appointed with green cabinetry, granite countertops, stainless steel appliances, and a gas range. Just beyond, a charming screened-in porch creates the perfect setting for morning coffee or al fresco dining. The spacious rear family room offers additional living space with sweeping bay views and sliding glass doors opening to the deck and fully fenced backyard, creating a seamless connection between indoor and outdoor entertaining. The main level includes a versatile bedroom ideal for guests or a home office, while upstairs, three generously sized bedrooms offer comfortable accommodations, including a spacious primary bedroom with beautiful Chesapeake Bay views. Additional highlights include a newer roof, new washer and dryer, generous outdoor entertaining areas, and a large storage shed is wired and has electricity. For boating enthusiasts, the nearby residents only marina offers boat slips reportedly available for $350 annually, providing convenient access to the Chesapeake Bay. Cedarhurst's waterfront community center, playground, beach, and picnic areas further enhance the neighborhood's coastal lifestyle. Whether as a primary residence or weekend retreat, 1244 Pine Avenue offers an exceptional combination of water views, generous outdoor living, boating access, and the tranquility of Shady Side's beloved Chesapeake Bay community.
Last check for updates: about 8 hours ago
Listing courtesy of Jenn Smira, (202) 280-2060
Compass, (202) 386-6330
Listing Team: Jenn Smira & Co | Fine Homes
Source: Bright MLS, MLS#MDAA2158194
Also Listed on Bright MLS.

Home Details for 1244 Pine Ave

Interior Features

Interior Details
Number of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 4Main Level Bedrooms: 1Number of Bathrooms: 2Number of Bathrooms (full): 2Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 2674 Square Feet
Appliances & Utilities
Appliances: Dishwasher, Disposal, Dryer, Microwave, Oven/Range - Gas, Refrigerator, Cooktop, Washer, Electric Water HeaterDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Heat Pump,ElectricHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Heat Pump
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Mantel(s)Has a Fireplace
Windows, Doors, Floors & Walls
Window: Bay/Bow, Double Pane Windows, Window TreatmentsFlooring: Hardwood, Carpet, Wood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: NoneFloors: Hardwood, Carpet, Wood
View
Has a ViewView: Water, Bay

Exterior Features

Exterior Home Features
Patio / Porch: Deck, Porch, ScreenedFencing: Back YardOther Structures: Above Grade, Below GradeFoundation: OtherNo Private Pool
Parking & Garage
Open Parking Spaces: 2No CarportNo GarageNo Attached GarageHas Open ParkingParking Spaces: 2Parking: Driveway,Asphalt
Pool
Pool: None
Frontage
Waterfront: Boat - Powered, Canoe/Kayak, Fishing Allowed, Private Access, BayNot on Waterfront
Water & Sewer
Sewer: Public SewerWater Body: Chesapeake Bay
Finished Area
Finished Area (above surface): 2674 Square Feet

Property Information

Year Built
Year Built: 1950
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Contemporary
Building
Construction Materials: Vinyl SidingNot a New Construction
Property Information
Condition: ExcellentParcel Number: 020715503203105

Price & Status

Price
List Price: $749,900Price Per Sqft: $280
Status Change & Dates
Possession Timing: Negotiable

Active Status

MLS Status: ACTIVE

Location

Direction & Address
City: SHADY SIDECommunity: Shady Side
School Information
Elementary School District: Anne Arundel County Public SchoolsJr High / Middle School District: Anne Arundel County Public SchoolsHigh School District: Anne Arundel County Public Schools

Agent Information

Listing Agent
Listing ID: MDAA2158194

Building

Building Area
Building Area: 2674 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.34 acres

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive Right To SellListing Terms: Cash, Conventional, FHA, Negotiable, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: MDAA2158194Water ViewWater View: Water, BayAbove Grade Unfinished Area: 2674

Additional Information

Internet Listing Display Prices: YSource Internet Automated Valuation Display: NSource Internet Consumer Comment: NSource Internet Entire Listing Display: YInternet Listing Display: Full Distribution - YesInternet Listing Display Days On Site: NInternet Listing Display Historical Prices: NSource Internet Address Display: Y

Price and Tax history

DateEventPrice
Sep 29, 2015
Source: N/A
Sold
$393,000
Aug 30, 2015
Source: Agent Provided
Pending
$399,000
Jul 24, 2015
Source: Agent Provided
PriceChange
$399,000
Price decreased by 2%
Jun 24, 2015
Source: Agent Provided
PriceChange
$407,900
Price decreased by 0%
Jun 12, 2015
Source: Agent Provided
PriceChange
$408,900
Price decreased by 0%

Around this home

What Locals Say about Shady Side

At least 26 Trulia users voted on each feature.

  • 97 % Say yards are well-kept

  • 96 % Say car is needed

  • 91 % Say it's dog friendly

  • 89 % Say kids play outside

  • 81 % Say people would walk alone at night

  • 76 % Say it's quiet

  • 76 % Say parking is easy

  • 73 % Say neighbors are friendly

  • 73 % Say there's wildlife

  • 71 % Say there's holiday spirit

  • 50 % Say they plan to stay for at least 5 years

  • 43 % Say there are community events

  • 32 % Say it's walkable to restaurants

  • 29 % Say streets are well-lit

  • 13 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Krmotto@gmail.com
    "the bay is so close, and the neighborhood is perfect for our small family. bike rides are fun, and good schools we think! "
    1
    Flag
  • Julie F.
    "We have nice parks and water access, and boat slips. Neighbors are friendly and watch out for each other "
    0
    Flag
  • Renee B.
    " If you want to live in a country or water setting this is a great area for just that. It is a relatively easy commute into DC, Annapolis or Baltimore. If you want box stores forget it! it's all about keeping it local down here. Enjoy the diverse community of friendly people who like to kayak, fish, sail, bike ride, power boat, motorcycle, hunt, eat local crabs & oysters, the arts, history at Captain Avery Museum, ride horses and so much more!! I gave the traffic an Excellent rating compared to the congested surrounding areas, every now and then you might get behind a farmers tractor who usually pulls over to let you pass! Public Transportation, there is a Park & Ride 15min away that has an excellent commuter bus into DC. School buses yes. Senior Citizen busses available. Community Involvement - Small 4th of July Parade, Oyster Festival, and just some good old fashioned neighborhood get togethers. "
    1
    Flag
  • Elena H.
    "For a quaint existence on the water where waking up to the tranquility of birds singing and going to sleep following an uninhibited view of the night sky are your drivers, this bucolic neighborhood is perfect! Ideal neighborhood for the boating crowd and a weekend home. "
    1
    Flag

Market trends in Shady Side

Last updated September 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
36
1MoM
Sourced by Trulia Market Trends

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5191 Spring Ave, Shady Side, MD
0.15
Single-Family Home
$469,000
04/21/26
4
3
1,632
1191 Poplar Ave, Shady Side, MD
0.31
Single-Family Home
$525,000
08/07/26
4
2.5
2,272
1194 Oak Ave, Shady Side, MD
0.19
Single-Family Home
$490,000
10/08/26
5
4
2,680
1191 Spruce Ave, Shady Side, MD
0.23
Single-Family Home
$400,000
05/15/26
3
1.5
1,296
5222 Spring Ave, Shady Side, MD
0.30
Single-Family Home
$500,000
07/31/26
4
3
1,730
4912 Mariners Dr, Shady Side, MD
0.30
Single-Family Home
$370,000
08/31/26
3
1.5
1,386
1195 Cedar Ave, Shady Side, MD
0.33
Single-Family Home
$674,900
11/05/25
4
2.5
2,710
1208 Oak Ave, Shady Side, MD
0.17
Single-Family Home
$381,000
01/09/26
3
2
1,062

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
1242 Pine Ave, Shady Side, MD 20764
0.01
$406,600
Studio
1
1,040
Off Market
1249 Poplar Ave, Shady Side, MD 20764
0.02
-
-
-
-
Off Market
1247 Poplar Ave, Shady Side, MD 20764
0.02
-
-
-
-
Off Market
1240 Pine Ave, Shady Side, MD 20764
0.02
$460,000
3
2
1,500
Recently Sold
1243 Pine Ave, Shady Side, MD 20764
0.02
$567,500
3
2
1,863
Off Market
1248 Pine Ave, Shady Side, MD 20764
0.03
$614,700
Studio
3
2,133
Off Market
1241 Pine Ave, Shady Side, MD 20764
0.03
$414,500
3
2
1,384
Off Market
1236 Pine Ave, Shady Side, MD 20764
0.04
$451,300
3
1
1,537
Off Market
1239 Pine Ave, Shady Side, MD 20764
0.04
$298,300
Studio
1
864
Off Market
5187 Park Ave, Shady Side, MD 20764
0.04
$399,800
Studio
2
1,450
Off Market
1254 Pine Ave, Shady Side, MD 20764
0.04
$625,700
Studio
3
2,268
Off Market
5185 Park Ave, Shady Side, MD 20764
0.04
$374,700
3
2.5
1,200
Off Market
1230 Spruce Ave, Shady Side, MD 20764
0.04
$449,700
1
1
720
Off Market
1237 Pine Ave, Shady Side, MD 20764
0.05
$309,700
Studio
1
1,144
Off Market
1234 Pine Ave, Shady Side, MD 20764
0.06
$312,100
2
1
736
Off Market
1226 Spruce Ave, Shady Side, MD 20764
0.06
$268,900
Studio
1
792
Off Market
1237 Spruce Ave, Shady Side, MD 20764
0.06
$79,250
-
-
-
Recently Sold
1250 Poplar Ave, Shady Side, MD 20764
0.06
$639,600
Studio
3
2,942
Off Market
5183 Park Ave, Shady Side, MD 20764
0.06
$392,900
Studio
2
1,428
Off Market
5184 Park Ave, Shady Side, MD 20764
0.06
$390,800
3
2
1,344
Off Market

LGBTQ Local Legal Protections

Jenn Smira, Compass, (202) 386-6330
Agent Phone: (202) 280-2060
The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information

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Frequently asked questions about 1244 Pine Ave

  • What is the estimated monthly payment for 1244 Pine Ave?
    Based on a $749,900 list price with 20% down at today's rates, the estimated monthly payment for 1244 Pine Ave in Shady Side, MD is approximately $4,684 (about $4,078 principal & interest, $531 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What do residents say about Shady Side?
    Residents describe Shady Side, MD as well-kept, dog-friendly, and quiet. Most residents say you need a car. See homes for sale in Shady Side, MD.
  • What are the closest schools to 1244 Pine Ave?
    The closest schools to 1244 Pine Ave in Shady Side, MD are Shady Side Elementary School (Pre-K, rated 7/10), Southern High School (rated 6/10), Southern Middle School (rated 8/10).
  • Does 1244 Pine Ave have air conditioning?
    Yes, 1244 Pine Ave in Shady Side, MD has air conditioning.
  • Does 1244 Pine Ave have laundry facilities?
    Yes, 1244 Pine Ave in Shady Side, MD has in-unit laundry.
  • Does 1244 Pine Ave have a yard?
    Yes, 1244 Pine Ave in Shady Side, MD has a yard.
1244 Pine Ave, Shady Side, MD 20764 is a 4 bedroom, 2 bathroom, 2,674 sqft single-family home built in 1950. This property is currently available for sale and was listed by Bright MLS. The MLS # for this home is MLS# MDAA2158194.